Regional Sales Manager

Enterprise Growth Market Position Overview

We are seeking a high-performing Regional Sales Manager to drive new business acquisition and strategic account expansion within a large, high-potential territory. This role is focused primarily on net-new prospecting (80%) into organizations with 5,000+ employees, with 20% dedicated to cross-sell and upsell opportunities within existing customers.

The ideal candidate is an experienced enterprise seller who excels in complex, multi-threaded sales cycles and is comfortable building relationships across C-suite and senior executive stakeholders.

• Own and execute a territory strategy for large enterprise organizations (5,000+ employees).
• Prospect, qualify, and drive net-new sales opportunities across the full sales cycle from initial engagement to negotiation and close.
• Lead multi-threaded pursuits, engaging stakeholders across HR, Talent, L&D, IT, Finance, and executive leadership.
• Execute account planning and expansion strategies within existing customers to drive cross-sell and upsell opportunities.
• Deliver compelling product presentations and business cases that articulate Cornerstone's differentiated value.
• Collaborate closely with Solution Consultants, Customer Success, Marketing, and Product teams to support deal progression.
• Maintain accurate pipeline forecasting and territory management through CRM.
• Represent Cornerstone as a trusted advisor and subject matter expert in HCM/Talent technology.

• 5+ years of enterprise sales experience targeting large, complex organizations.
• Proven track record of consistent performance and quota achievement in SaaS, HR tech, HCM, or related enterprise technology.
• Demonstrated ability to lead multi-threaded, long sales cycles and engage C-level and senior executive stakeholders.
• Strong business acumen with the ability to connect solutions to strategic business outcomes.
• Excellent communication, presentation, and negotiation skills.
• Ability to manage a large, high-volume territory with strong prioritization and pipeline discipline.
• High degree of self-motivation, accountability, and ownership.

• Experience selling HCM, Talent, Learning, or Workforce
• Understanding of enterprise HR processes and digital transformation initiatives.
• Background working with global enterprises and matrixed organizations.